Planned Giving Software: How to Choose the Right Tool

Key Takeaways

• Three Distinct Categories: The term "planned giving software" covers three functionally different categories of tools. Conflating them often leads to buying the wrong one.
• The Silent Bequest Problem: An astounding 64% of legacy pledgers never actively notify the charity that they have included them in their will. The right software solves this tracking issue immediately.
• Focus on Workload: Whatever you choose should reduce total staff workload. A second system to manually maintain alongside your CRM is a net loss for a lean team.

Quick Answer

"Planned giving software" is not one category of tool. Rather, it spans donor-facing education and gift-building tools, internal pipeline and stewardship tracking, and gift calculation engines for complex gift types. 

Therefore, start by identifying where your current process actually breaks down, not by comparing feature lists. Avoid any tool that requires a dedicated gift-planning specialist to operate if you do not have one on staff already.

In This Guide

• Why this decision matters more for smaller teams
• "Planned giving software" and its three different meanings
• The question to start with
• Questions worth asking any vendor
• What this looks like in practice
• Frequently asked questions

Why This Decision Matters More for Smaller Teams

"Planned Giving Software" Means Three Different Things

Before comparing vendors, it helps to know which problem you are actually trying to solve. The term "planned giving software" covers tools that do not do the same job. A glossy demo of one category can look appealing even if it is the wrong type of tool for your situation.

Let's walk through the three main use cases of planned giving software.

1. Donor-Facing Education and Gift-Building Tools

These tools sit on your website and let supporters explore gift options, build simple wills, or document bequest intentions directly. The best versions explain gift types (like bequests or beneficiary designations) in plain language and let a donor move from "curious" to "documented" without ever calling your office.

• Best fit for: Organizations that want to generate and capture donor interest at scale without requiring staff time per prospect.

2. Internal Pipeline and Stewardship Tracking

Next, these tools help your team see who has expressed interest, where each prospect sits in the cultivation process, and when a gift was actually documented. They are usually layered on or integrated with your existing donor database system rather than replacing it.

• Best fit for: Organizations that already have donor interest and conversations happening, but no clean way to track status, follow-up dates, or documented gifts.

3. Gift Calculation and Illustration Engines

These engines run the technical numbers behind more complex gift types, such as charitable remainder trusts and gift annuities. They produce the illustrations a donor or their financial advisor needs to evaluate a specific proposal.

• Best fit for: Organizations actively soliciting complex life-income gifts at a meaningful volume. This typically describes a smaller, more specialized subset of nonprofits with an existing major-gift function.

Most small and mid-sized nonprofits only need the first two. The third matters mainly once an organization is routinely working with donors on trusts and annuities, which is a later-stage problem for most teams.

The Core Question to Start With

• "We have no idea who is thinking about this." → You need a donor-facing tool that surfaces interest, not just a brochure that sits unread on a webpage.
• "Someone mentioned it to a board member two years ago, and we never followed up." → You need pipeline tracking, not another donor-facing tool.
• "We do not have anyone who knows how to explain the different gift types." → You need a tool that does the donor education for you in plain language without requiring a specialist on staff.
• "We have interest, but no visibility into what has actually been documented." → You need a tracking dashboard, not more outreach to generate even more untracked interest.
• "We're fielding real questions about trusts and annuities and lack the tools to run the numbers." → This is the point at which a calculation and illustration engine becomes relevant.

Questions Worth Asking Any Planned Giving Software Vendor

Now that you know a bit more about what you're looking for in a planned giving solution, consider the following inquiries to bring to any prospective software vendor.

1. Does this require a dedicated gift-planning officer to operate? If yes, and you do not have one, the tool is solving a problem you do not currently have the staff to run (no matter how capable the tool itself is).
2. Does it integrate with, or replace, our existing CRM? A second system your team has to check separately tends to get checked less and less often over time, eventually stopping being used at all.
3. Can a donor actually use it themselves without calling our office? Self-serve donor tools only help if donors will actually use them unassisted. Ask to see the actual donor-facing experience, not just the admin dashboard.
4. What happens to a documented gift once it is made? Make sure there is a clear, visible record your team can see and act on. It should not just be a form submission that disappears into an inbox.
5. What does it cost at our actual scale? Per-seat pricing built for a five-person gift-planning department often does not translate sensibly to a one- or two-person team. Ask specifically about pricing for your size.
6. How long does implementation actually take? A tool that takes months to configure properly is a meaningfully different commitment than one a small team can get running in a matter of days. This matters disproportionately when you lack dedicated IT staff.

What Small-Team Planned Giving Actually Looks Like

Frequently Asked Questions